1-Methylimidazole → 3-(2,4-dichlorophenoxy)-1-nitro-1-(tetrahydro-2H-1,3-thiazin-2-ylidene)-2-propanone

HRID 329160

Reaktionsgleichung

Reaktionsgleichung von HRID 329160
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6](Cl)=[O:7].CN1C=CN=C1.[N+:20]([CH:23]=[C:24]1[NH:29][CH2:28][CH2:27][CH2:26][S:25]1)([O-:22])=[O:21].[O-][Si]([O-])=O.[Mg+2]>O1CCCC1.C(Cl)Cl.O>[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6](=[O:7])[C:23]([N+:20]([O-:22])=[O:21])=[C:24]1[NH:29][CH2:28][CH2:27][CH2:26][S:25]1

Komponenten

8

Edukt 4

HCID 13901-MethylimidazoleHCID 428532-nitromethylenetetrahydro-2H-1,3-thiazineHCID 61680MAGNESIUM SILICATE (synthetic)HCID 69887(2,4-Dichlorophenoxy)acetyl chloride

Produkt 1

HCID 867346973-(2,4-dichlorophenoxy)-1-nitro-1-(tetrahydro-2H-1,3-thiazin-2-ylidene)-2-propanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

A solution of 7.2 g of 2,4-dichlorophenoxyacetyl chloride in 20 ml of tetrahydrofuran was added dropwise to a solution of 2.5 g of 1-methylimidazole in 80 ml of tetrahydrofuran at 0.5°. The resulting slurry was stirred for 30 minutes at 5°, then 4.8 g of 5B was added all at once. The mixture was stirred overnight. Then 0.5 equivalent mole of the imidazole complex in 50 ml of tetrahydrofuran was prepared and added at 5°. The stirred mixture was allowed to rise slowly to room temperature, and stirred overnight. The solvent was stripped; the residue was treated with 1:1 volume mixture of water and methylene chloride. The phases were separated, the water phase was extracted with methylene chloride, the methylene chloride solutions were combined, washed with water and saturated salt solution, dried (MgSO4) and the solvent was stripped to give an oil. The oil was passed through Florisil to give a mush, which was triturated with pentane to give 3-(2,4-dichlorophenoxy)- 1-nitro-1-(tetrahydro-2H-1,3-thiazin-2-ylidene)-2-propanone (5C), as a pale yellow solid, m.p.: 164°-164.5°.

Aufarbeitung

  1. stirringThe mixture was stirred overnight
  2. additionadded at 5°
  3. customto rise slowly to room temperature
  4. stirringstirred overnight
  5. customThe phases were separated
  6. extractionthe water phase was extracted with methylene chloride
  7. washwashed with water and saturated salt solution
  8. dry with materialdried (MgSO4)
  9. customto give an oil
  10. customto give a mush, which
  11. customwas triturated with pentane

Quellen und Nachweise

ORD-Eintrag
ord-a7d939efcb5046068f80b05f6afc6d68
Quelldatensatz
uspto-grants-1977_04
Patentnummer
US04020061

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